What Can You Say About a Guy Who Loved Newspapers, New York, and Tinned Sardines? Final Thoughts on Legendary Editor Peter Kaplan

Peter Kaplan, 1954-2013. At the time of his death, he was the editorial director of Fairchild Fashion Media.

When Peter Kaplan, the editor in chief of theNew York Observerfrom 1994 to 2009—and my boss for nearly 10 of those years—died last month at the age of 59, my editors atVanity Fairasked if I would write a remembrance. I immediately accepted. I’ve been blessed with exceptional editors throughout my career, but Kaplan influenced me more than any other. He became my friend and, at times, a father figure, and I wanted to honor him. What I hadn’t realized, however, was that I was still in denial about his death. For almost a week I sat paralyzed at my computer screen staring at a jumble of memories, unable to make them add up to anything. When the words finally came, Peter’s funeral had passed, and the media had moved on to other stories. So I am extremely grateful toVanity Fairfor bearing with me and understanding that grief does not always respect the news cycle.

In the weeks before Peter Kaplan lost his gallant__ __battle with lymphoma, his friends and family resolved to keep his spirits up by peppering him with get-well wishes delivered via text, e-mail, phone, and in person. As a neurobiologist friend of his put it, we needed to become the “dorsolateral prefrontal cortex for him”—the part of the brain that overrides fear with optimism.

I had a good idea what that meant. When you write on deadline, there are few things more terrifying than staring at a blank computer screen with a head full of reporting and ideas and no concept of how to get them on the screen. The coffee or bananas or Ritalin that you depend on for mental stamina and clarity are not working, and the clock in the corner of your computer screen keeps reminding you that you are one less minute away from the end of your career. E. L. Doctorow was not exaggerating much when he called writing “a socially acceptable form of schizophrenia.”

When I was working for Peter at the New York Observer and could not quell that fear, I joined the procession of writers and editors stalking back and forth between their desks and his office on the well-worn fourth floor of the paper’s East 64th Street townhouse, hoping to see his door ajar and him inside. The scrum for Peter’s attention spiked on Mondays and Tuesdays, the days the paper closed its weekly issue and the days that his workload was the most demanding. Begging or bartering our way into his office, most of us wanted the same thing: to let him into our heads so that he could steamroll our fear and self-doubt with his dazzling intelligence and enthusiasm.

In December of 1998, I had been assigned to write a cover essay for something called the Observer 500, a special issue that attempted, pre-Nate Silver, to rank celebrities by the number of gossip-column mentions they’d received over the course of that year. It was a terrible idea—mine, by the way—because there were no surprises for pages and pages, and little meaning to draw from the results. Prior to joining the paper in 1993, I’d worked as a gossip columnist at the New York Post’s notorious Page Six column, so I knew how that sausage was made, but I couldn’t figure out how to make the essay add up to something more than just a dry bunch of numbers.

I headed to Kaplan’s office, which was a hoarder’s wet dream of precariously stacked newspapers, books, and illustrations by the paper’s great artists, Drew Friedman, Bob Grossman, Philip Burke, and Victor Juhasz, among them. Perhaps because it was often difficult to find a place to sit, I found myself standing face-to-face with Peter, who was wearing his usual work uniform of a blue oxford shirt, khakis, rep tie, and scuffed shoes. In what would be a clear violation of most companies’ HR policies today, he had his hands clamped on my shoulders and was squeezing my trapezius muscles. Hard.

“Frank*!*” Peter said as he squeezed tighter and stared at me through his round tortoise shell spectacles. “Listen to me. Listen to me. Listen to me!” He often spoke to me in the same way he wrote headlines—with plenty of ironic exclamation points and an urgency that suggested he was trying to keep me from losing consciousness. “It’s simple,” he said. “This is the year that the government got into the gossip business.” In September of that year, Kenneth Starr, who investigated the Clinton administration during the Monica Lewinsky scandal, had released his salacious report about the president’s affair, which would pave the way for Clinton’s impeachment. The point, Peter explained, was that Washington no longer needed a Walter Winchell to do its dirty work.

One of the most satisfying moments in long-form journalism is when you crack the thesis sentence or paragraph on which you hang your story. Some editors call it “the nut ’graph.” Kaplan called it “the billboard,” and along with the headline, he considered the billboard the most crucial part of the story. No one was better at generating them. He had a special gift for seizing what you might also call a meme and then advancing it intellectually.

As he slowly released his grip on my shoulders, my head was buzzing, partially due to a loss of circulation but mostly because Peter had handed me a beautiful billboard, one that tied the national scandal to the New York gossip trade. The ideas that were haphazardly circling my head began to line up like a perfect Tetris game. I ran back to my desk and wrote the piece as if it had been dictated to me.

Kaplan was a fan of classic Broadway musicals. The Music Manwas one of his favorites, and he had the persuasive powers of that play’s lead character, Harold Hill. (Every leader worth his salt has a little huckster in him.) Again and again, he convinced us that what we were doing at the Observer was tremendously important—and an adventure. Author Warren St. John once recalled that while struggling with a story about how the Lewinsky scandal had revived the career of hack journalist Geraldo Rivera, Kaplan “had me convinced after twenty minutes that I was writing [Norman Mailer’s] TheArmies of the Night, that I was writing one of the great snapshots of our time and culture.

Another example: shortly before Jay Stowe, one of the writers of the paper’s “Off The Record” media column, left for a crucial interview with Teflon quote–spouting Time Inc. editor in chief Norm Pearlstine, Kaplan called the nervous reporter into the office to provide some last-minute inspiration. Pouring his writer a stiff plastic cup full of bourbon—Peter’s drink of choice—Kaplan launched into a soliloquy. Stowe, who’s now the editor in chief of Cincinnatimagazine, recalls him “quoting from Henry Luce’s American Century before sending me off.” When the fortified Stowe subsequently asked the Time Inc. editor “what separated him from being a glorified marketer,” Pearlstine walked out of the interview. “I thought I was going to get fired,” Stowe says, but when he went back to the office and explained what had happened, “Kaplan let out an explosive guffaw, patted me on the back, and said something like, ‘Attaboy!’ ”

The editing at the Observer was superb, but when Kaplan got personally involved in editing a story, he could make the writer look too good. In October 2001, I covered that annual ritual of profane and brutal humor, the New York Friars Club roast, at the Hilton. That night, stand-up Gilbert Gottfried made comedy history by telling “The Aristocrats”—one of the profession’s oldest and filthiest jokes—prompting arguably the first cathartic moment of laughter in the city since the terrorist attacks of 9/11. Kaplan was a connoisseur of comedy, particularly of the vintage vaudevillian variety the Friars embodied—reporting on the roast, in unexpurgated form, was a tradition at the paper—and there’s a lot of his handiwork in that piece, including the story’s most memorable line. To this day, I would be incapable of writing it myself. Peter knew opera almost as well as he knew A Night at the Opera, and he inserted a line that labeled Gottfried’s performance “the comedy equivalent of the B-flat below high C that [soprano] Leontyne Price had sung at Carnegie Hall,” referencing a recital that had taken place around the same time as the roast. The story landed me a talking-head spot in the 2005 documentary The Aristocrats, and one of the first things the director, Paul Provenza, asked me to talk about was the Price reference. Somewhere footage exists of me blushing and explaining that my editor had written the line.

Two of Peter’s favorite words and phrases were “giddy” and “tremendous fun,” and he had a tremendous smile to match, one that suggested he was replaying a magnificent joke in his head. Especially during the pre-9/11 years, there were times when working at the paper felt like an extended endorphin rush—My Favorite Year with headlines—although those staffers who needed more structure and decorum in their lives would probably liken the place to One Flew Over the Cuckoo’s Nest. Kaplan’s miniscule budget never diminished his ambitions, and his enthusiasm for where the paper could go and what it could achieve was infectious.

During a 2009 appearance on the PBS talk show Charlie Rose, a program Kaplan had himself once produced, Peter said, “The New York Observer was a) meant to diagnose power in New York; and b)”—there was usually a b)—“meant to, in a weird way, be a Rashomon to the *New York Times.”*He respected the Times immensely, but, having worked there as a TV reporter, he understood its flaws. He once told me that his experience there was like driving a tank: “You have tremendous firepower,” he said. “But your field of vision is limited, and you’re a sitting duck.”

Peter saw New York and the world in Cinemascope and Technicolor, and, under him, the Observer became a paper that combined strong reporting, interpretation, and writing to make news, and to advance the hot topics of the time. And what a time it was. In the 1990s and early 2000s, history was repeating itself as farce and producing characters befitting a Tom Wolfe novel: Bill Clinton, Martha Stewart, Harvey Weinstein, John F. Kennedy Jr., Tina Brown, Jerry Speyer, Rudy Giuliani, Jennifer Lopez, Judith Regan, Sandy Weill, Larry David, Howell Raines, and Jayson Blair. The Hamptons were hot, Botox and Seinfeldand Ugg Boots were cool, and the characters of Candace Bushnell’s Sex and the City column were rewriting the rules of coitus metropolis.

Peter never liked to make that scene. He’d grown up in New Jersey and made his home in Larchmont, in Westchester, and, despite having gone to Harvard where he roomed with Robert F. Kennedy Jr., he preferred to be an outsider. They made the best editors he said. So he sent us out into the city and to the Hamptons to gather intelligence. We were his wisecracking band of rebel fighters fighting a war against hubris, launching smart bombs at the Times’s tanks and other institutions that took themselves too seriously. And we relied on Kaplan’s breathtaking knowledge of the past—politics, show business, movies, show tunes; Bob Dylan was about as contemporary as his musical tastes got—to explain the present and predict the future. The complaint was that we were snarky, but that’s what people say when they can’t refute the reporting.

We rankled the New York Establishment plenty, and I’m convinced that is why Peter was denied the accolades he was most certainly due while he was alive. He more than earned his spot in the pantheon of great editors, where *Esquire’*s Harold Hayes; Kaplan’s mentor, New York magazine founder Clay Felker; and the New Yorker’s Harold Ross reside. Another tribute: the current media establishment, and the groundbreaking upstart companies and Web sites that challenge it, are seeded with men and women who worked for Peter.

If you worked for Peter, you also couldn’t help but notice the parallels between him and another innovator, David Letterman. Kaplan was fascinated by the late-night talk-show host, and had written some of the earliest and best profiles of him for Esquire and Rolling Stone. Upon Peter’s arrival, Letterman became a recurring character in the Observer’s pages as well and, for a while, his shows were obsessively deconstructed in editors’ meetings. In John Homans’s tribute to Kaplan in New York magazine, he wrote that “Letterman…was Peter’s doppelgänger: flawed, self-critical, bested by the more conventional host, but indomitable.”

Laughter was equated with praise in the Kaplan universe—he loved to laugh, and if you got him to suck air and wheeze a little bit, you knew he wasn’t just being polite—and so, the Wednesday editors’ meetings, where 8 to 10 of us would squeeze into his office to discuss the coming issue, carefully moving papers and memorabilia so that we might find a place to lean or sit, could devolve into This Is the End–style zing competitions in which the comments got personal and lacerating. Even Peter took some hits, and though more than once irritation crossed his eternally boyish face, he gave us more rope to hang ourselves than any other editor I’ve known.

The jokes were an extension of the culture of honesty that Kaplan cultivated at the Observer. When he was angry, you knew it. The door to his office would be slammed in your face with a curt, “Not now!” and once, in a fury, Kaplan swept into my office and started tossing papers, books, and CDs from my desk out the window onto East 64th Street. He stopped when I noticed that a woman with a baby carriage was in front of the Observer’s townhouse looking angrily up at us. And then cowering on each side of the window, we both dissolved in laughter.

And though there was no place in his paper for sentimentality, Kaplan could be remarkably empathetic. In early 1997, I became a father for the first time and my work suffered. It wasn’t just the fatigue of dealing with a colicky newborn. Something larger had happened. The New York that I loved seemed a grayer, less vibrant place. It was a dangerous malaise to have at a paper that found endless inspiration in the city’s constant, cacophonous evolution.

One afternoon, Kaplan invited me to have lunch with him at the Gardenia, a Madison Avenue diner just a few blocks north from the New York Observer’s East 64th Street offices. Kaplan was a connoisseur of diners, and, for a period, the Gardenia was his Stork Club, his second office where he could escape from the line outside his door. His lunch order was as predictable as his work clothes: canned fish—sardines or tuna—on rye toast, split pea soup, and coffee. That day, I described my malaise. “It’s simple,” explained Peter, who was the father of four children: I had participated in the creation of something that was far superior to anything I would ever write.

That sums up my experience at the Observer, too.

One of the last texts that Peter sent me had to do with his doppelgänger, Letterman. Like many of his friends, I’d been sending Peter jokes in an effort to heal him with the best medicine.

Somewhere in the back of my mind, I remembered a friend with ties to comedy telling me what he swore was Letterman’s favorite joke. I texted Peter my recollection of it:

“A man walks into a Cadillac dealership and makes a beeline for a brand new Escalade. As he stands admiring the luxury SUV, a salesman approaches and says, ‘Sir, are you thinking of buying a Cadillac today?’ To which the man responds, ‘Oh, I am going to buy a Cadillac today, but if you must know, I’m thinking of pussy.’ ”

Peter didn’t always respond to my texts—during his time at the Observer, he was notorious for not returning phone calls—but this time he did. And as was usually the case, Peter taught me something I didn’t know.

Dear Frank

Letterman has always had a weakness for Tom Dreesen who knows how to make him laugh and has his favorite joke, which is close to that in concept but much longer. Will tell it to you. Much Love Peter